Director of Finance

Remote from: USA
Salary, yearly, USD: 220,000 - 280,000
Department: Finance & Accounting
Employment type: Full Time,
Job posted: 28 May 2026
Apply before: 28 Jun 2026
Experience level: Director
Views / Applies: 39 / 12

Tremendous helps businesses send rewards and payouts to people around the world.

Financial Services
2010

AI Summary

Tremendous is seeking a Director of Finance to lead financial planning, modeling, and strategic analysis. The role involves creating external financial narratives, owning FP&A, supporting deal desk pricing, driving forecasting, and building the finance function. Ideal candidates have investment banking and growth-stage startup experience, with a focus on complex B2B deals. The company is profitable, remote-first, and values high-documentation, low-meeting culture. This position offers competitive pay, equity, and comprehensive benefits.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role requires deep expertise in investment banking, FP&A, and deal structuring at a growth-stage startup, with a high degree of autonomy and complex financial modeling. The ambiguity and need for strategic decision-making elevate the difficulty to a 4.

Salary Analysis

AI Insight The offered salary range of $220,000 to $280,000 is competitive and above the market median for a Director of Finance role, reflecting the high level of responsibility and the company's profitability. The total compensation including equity and benefits makes this an attractive package.

Key Skills

Financial Planning and Analysis Investment Banking Financial Modeling Deal Structuring FP&A Strategic Analysis Startup Finance Enterprise Sales Support Data-Driven Decision Making Team Building

Cover Letter Sample

I am excited to apply for the Director of Finance position at Tremendous. With over 2 years in investment banking and 4+ years leading finance at growth-stage startups, I have a strong track record of building complex financial models and structuring enterprise deals. Your description of a low-meeting, high-documentation culture aligns perfectly with my work style, and I am eager to bring my analytical rigor to a profitable, fast-growing company.

I have been involved in transactions exceeding $100MM and have deep experience with FP&A, forecasting, and data-driven optimization. I thrive in environments where I can build functions from the ground up and contribute to strategic decision-making. Tremendous's innovative payout platform and strong culture make it an ideal place for me to apply my skills.

I look forward to discussing how I can help drive financial excellence at Tremendous.

Possible Interview Questions

Can you walk me through a complex financial model you built from scratch? What were the key assumptions and how did you validate them?

I built a revenue model for a B2B SaaS company that involved multiple revenue streams (subscription, usage-based, and professional services). I started by documenting assumptions from historical data and market research, then built a dynamic model in Excel with scenario analysis. I validated assumptions by cross-referencing with industry benchmarks and conducting sensitivity analysis.

Describe a time you had to structure a complex enterprise deal. How did you balance financial soundness with strategic goals?

At my previous startup, we had a large enterprise customer requesting a custom pricing structure. I worked with sales and legal to create a tiered pricing model that included volume discounts and multi-year commitments. I analyzed the customer's usage patterns and lifetime value to ensure the deal was profitable while aligning with our strategic goal of securing a long-term partnership.

How would you approach forecasting for a company with multiple complex revenue streams?

I would start by segmenting revenue streams (e.g., transaction fees, subscription, gift card margins) and building separate models for each. I'd use historical data to identify trends and seasonality, then incorporate leading indicators like sales pipeline and customer churn rates. I'd also run Monte Carlo simulations to account for uncertainty and present a range of outcomes.

Given that Tremendous is profitable without outside investors, how would you manage financial planning differently compared to a VC-backed company?

Without external pressure, I would focus on sustainable growth and profitability metrics rather than growth-at-all-costs. I'd emphasize cash flow management, efficient capital allocation, and long-term strategic investments. The financial story would be tailored to internal stakeholders and potential acquirers, highlighting stability and profitability.

Tell me about a time you used data to identify an inefficiency or opportunity. What was the outcome?

At a fintech startup, I analyzed customer acquisition costs across channels and found that one channel had a significantly higher ROI. I recommended reallocating budget from underperforming channels, which reduced overall CAC by 20% while maintaining lead volume. This data-driven decision improved marketing efficiency and contributed to better unit economics.

Tremendous is the global platform built for businesses to send thousands of payouts to anyone, anywhere, for free. We’re trusted by 20,000 organizations like Atlassian, MIT, and United Way to deliver gift cards and money to millions of recipients worldwide.

Our customers (researchers, marketers, HR teams, nonprofits, and platform businesses) rave about how fast and easy Tremendous is to use. Check out our ratings on G2.

Tremendous is profitable and growing without outside investors. We’re a fully remote, high-documentation, low-meeting culture, which means more time for what matters in both your professional and personal life. The team agrees– our employee NPS is in the high 80s.

What you’ll do

Create the external story: Package our business model and financials for external parties—whether that’s potential partners, acquirers, or other stakeholders. Your investment banking background will be crucial here.
Own FP&A: Oversee and maintain detailed financial models that capture our complex revenue streams. Work with the Finance and Data teams to document assumptions, outputs, and scenarios in a way that’s both rigorous and understandable.
Support Deal Desk: Help structure and price of complex enterprise deals. Work cross-functionally with sales, legal, and product to ensure deals are both financially sound and aligned with our strategic goals.
Drive forecasting and planning: Keep our financial forecasts updated, accurate, and defensible. Automate wherever possible.
Explore and optimize: Dig into our data to identify trends, inefficiencies, and opportunities. Bring curiosity and analytical rigor to everything you do.
Build the function: As we grow, you’ll have the opportunity to build out the finance team and establish best practices for financial operations.

What you’ll bring

2+ years in investment banking: You’ve spent time in IB and know how to build complex financial models, tell a compelling financial story, and think about businesses from a strategic perspective.
4+ years at growth-stage startups (ideally at least one FinTech): You’ve led finance teams and owned the FP&A model at fast-moving startups and understand the pace and ambiguity that comes with it. You’re comfortable making decisions with incomplete information.
$100MM+ transaction involvement: You’ve been intimately involved with multiple startup transactions, including at least one (either an investment or an acquisition) $100MM+
Deal structuring experience: You’ve worked on pricing and structuring complex enterprise deals, ideally in a B2B context.
Modeling obsessive: You genuinely enjoy building financial models and can get lost in Excel or other modeling tools. You care about getting the details right.
Naturally curious: You ask “why” and “what if” constantly. You’re drawn to complex problems and enjoy digging into data to find answers.
Runway experience (preferred): You’ve used Runway for FP&A and know how to leverage it effectively.
Low ego, high impact: You’re excited to do the work yourself rather than delegating everything.

What’s cool about the role

No board theater: We’re profitable with no outside investors, which means no board meetings and no wasted time on investor relations. Your work will focus on actual financial planning and analysis.
Complex, interesting business: Our revenue model is sophisticated and multi-faceted. If you like easy, simple SaaS businesses, this isn’t the role for you. If you like intellectual challenges, you’ll love it here.
Competitive pay and equity. Base salary for this role: $220,000 to $280,000.
Real benefits. 100% covered health (US), unlimited PTO, 12-16 weeks paid parental leave.
Fully remote. Work from anywhere in the Americas.
Great culture. Read more about how we work in our public handbook.